


He's so Obssessed with Me

by cozypancakes



Category: Community (TV)
Genre: Humor, Jeff is great at lying to himself, M/M, Romance, his ego can't handle not being the center of attention, light smut at the end
Language: English
Status: Completed
Published: 2020-05-17
Updated: 2020-05-17
Packaged: 2021-03-03 02:15:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,599
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24237154
Author URL: https://archiveofourown.org/users/cozypancakes/pseuds/cozypancakes
Summary: The Dean's experience with Domingo makes him promise to not make Jeff uncomfortable by randomly touching him all the time. Jeff is at first unsettled by this but realizes that no one, especially not the Dean, can resist him. He goes to great lengths to prove that point.
Relationships: Dean Craig Pelton/Jeff Winger
Comments: 34
Kudos: 222





	He's so Obssessed with Me

“Another crazy week at Greendale,” Jeff proclaimed, walking into the Dean’s office.

“Oh, Jeffrey,” the Dean greeted him. “Yes...it was  _ quite  _ a week.” 

Jeff looked at the Dean. He couldn’t help but notice that he was much more subdued than usual. Losing his position on the school board was still weighing on him. And because the Dean was one of his friends, Jeff felt affected by his sad mood. That was the only reason he’d planned to ask the Dean to dinner tonight. 

“I’m glad you stopped by, Jeffrey. I’ve been meaning to have a word with you.”

“What about?” Jeff asked. He sat down on the couch. Once they got whatever work thing the Dean wanted to talk about out of the way, Jeff would ask him to dinner.

“Well,” the Dean began. The Dean stood up from his seat and walked around the desk. He leaned against the edge, avoiding Jeffrey’s eyes. Jeffrey frowned in confusion. The Dean seemed nervous. “As you know, I had to have Domingo pretend to be my partner for the board position.” 

“Right,” Jeffrey said. He bit back the urge to say something snide about Domingo.

“Well, I don’t know if you noticed, but it was quite annoying having Domingo right there-” the Dean gestured to over his shoulder “-all hours of the day. His eyes constantly on me and always needing to touch me…”Jeff was sympathetic to the Dean’s complaints. He’d noticed how Domingo had been overly affectionate with the Dean. It hadn’t sat well with Jeffrey whenever he’d seen them together. Now he understood that he’d picked up on the Dean’s discomfort and, as a friend, had been unnerved by it. “And now that the whole charade is over, I realize how big of a hypocrite I am!”

“Um, I don’t follow,” Jeff admitted. 

“You’re sweet, Jeffrey.” The Dean raised a hand, as if going to pat him, but then quickly pulled back. “See! I do exactly what Domingo does!” the Dean exclaimed. “But worse because I asked Domingo to pretend to be my partner. You’ve made your feelings towards me abundantly clear.”

“Oh,” Jeff breathed out. Now he understood. The Dean was apologizing for all the lingering touches and leering looks. Jeff shifted in his seat. 

“Yes, exactly. I, of course, ignored all your rejections because...well, I’m an optimist,” the Dean said, shrugging apologetically. “But after being on the receiving end, I can’t keep making you so uncomfortable Jeffrey.” He stood up and stretched out his hand to Jeffrey. “I promise, from now on, we’ll have a completely professional relationship.”

Jeff stared up at the Dean. His mind was still trying to wrap his head around all this. He’d spent all day going back and forth on whether to be a nice guy and invite the Dean for dinner and now...the Dean was promising him what he’d always wanted. 

Jeff slowly stood up and shook the Dean’s hand. He forced a smile on his face as he watched the Dean beam up at him. 

* * *

By the time the Save Greendale Committee met on Monday, Jeff was perfectly fine with what the Dean had said last week. Not that he spent all weekend going back and forth about it. Well, he had been a bit unnerved to think of a reality where the Dean wasn’t fawning all over him. But once the initial shock wore off, Jeff had gone about his weekend as normal. He even fit in an extra workout, or three.

And this morning, while he’d been meticulous choosing what shirt to wear, Jeff had had a realization. The Dean may have all the intention to stop drooling over Jeff, but that didn’t mean he would be successful. Afterall, Jeff was the hottest person on campus. The Dean would get over the Domingo fiasco soon enough and be back to touching Jeff whenever the opportunity presented itself. 

So with things perfectly normal, Jeff was fine with leaning back in his seat and listening to Annie and Britta recount their weekends. Frankie walked in a few minutes later and officially started the meeting. Jeff let his mind tune in and out of the conversation. He did however remain in his casually leaned back position, hands interlocked in front of his chest so as best to draw attention to his biceps. 

When the Dean finally did stroll in near the end of the meeting, Jeff had to fight back physically bolting up in excitement. Finally, he’d get to prove that no one could resist his sex appeal! 

“Happy Monday everyone!” the Dean said in greeting. He went to stand in between Abed and Britta, casually placing his hands on the backs of their chairs. 

“I’m pretty sure that’s an octagon,” Britta grumbled. Jeff broke his practiced aloofness to give Britta a confused look along with the rest of the group. 

“I think you meant oxymoron,” Frankie gently suggested. Wow, Jeff had no idea how Frankie had managed to connect the Britta dots for that one. 

“Oh, but Mondays are happy because I get to see all of you again,” the Dean explained. There was a course of aw’s around the table. Leave it to the Dean to put a happy and sentimental spin on the worst day of the week. The Dean smiled around at the group but didn’t look at anyone in particular. Jeffrey wasn’t bothered though. The Dean always touched his shoulder/chest before exiting a room. “Anyway, I came to grab Frankie for a meeting with the school board. I figured we’d carpool over.” 

“Good idea,” Frankie said. She quickly gathered her things and walked out with the Dean.

“Have fun!” Annie called after them. “Lunch?” she asked the group. 

Jeff was on autopilot as he followed the group out. The Dean hadn’t even made eye contact with him. And not in an I-am-too-embarrassed-to-look-you-in-the-eye kind of way. This was different, more casual. So the Dean was more determined to keep his promise than Jeff had realized. That was fine. Jeff knew he wouldn’t be able to hold out for long. 

* * *

Jeff started off slowly. Mainly because he didn’t think it would take much to make the Dean crack. So the next day he showed up on campus smelling of his most expensive cologne and with two extra buttons left undone on his shirt. 

As he walked to the library, he was definitely aware of people’s heads turning in his direction. Yes, this was definitely going to work. He walked into the study room and took his seat. 

“Wow,” Britta complained. She waved a hand in front of her face. “Did you use the whole bottle today?” 

“What? No,” Jeff replied. He fought the urge to sniff himself. He may have put on a  _ little _ more than usual, but Britta was obviously exaggerating. 

“Um, Jeff,” Annie said. He looked over at her. “I think you forgot some…” she gestured vaguely at her chest and then blushed. Jeff did his best to keep a straight face as he raised an eyebrow as if confused. “Nevermind,” Annie mumbled, looking away. At least Annie had had the expected reaction. Britta never outwardly admitted he was the sexiest man on campus so he wouldn’t be deterred by her reaction. 

It would be a matter of time before the Dean walked in and made a move on him. Jeff’s smug mood lasted all the way through lunch. He kept assuming that the Dean would show up at some point. He could hardly recall a day when the Dean hadn’t found some excuse or another to say hello. 

By the time his final class ended, Jeff was considering all the possible excuses he had to go by the Dean’s office. He decided against it though, forcing himself to walk straight to his car. Tomorrow he’d definitely bump into the Dean, no reason to rush it. 

* * *

Two days. Two whole days had gone by and Jeff had yet to see the Dean. This had to be some kind of record. He’d never gone this long without bumping into the Dean. Jeff had gone so far as to look for him yesterday but he’d had no luck. Today was going to be different. He was going to see the Dean today and, for good measure, he took his secret weapon with him. 

The plan was simple. He was going to wait right outside the Dean’s office while he did his morning announcements and then corner him. Sadly, he didn’t take into account running into Annie and Britta on his way there. 

“Oh my god,” Britta exclaimed. 

Jeff let out a deep sigh and turned around. Both Annie and Britta eyed him from head to toe. Annie blushed while Britta scowled at him. It wasn’t as dramatic as the pair of freshmen who’d run into a wall while doing a double take of him, but it was still something. 

“Why are you wearing those?” Britta asked. She briskly walked up to him and took his aviators off his face. 

“Hey, those are expensive,” Jeff complained. 

“Are you on anxiety meds again?” Britta asked. 

“No.” This seemed to give Britta pause. She glowered at him, probably going over any possible terms from her psychology book she could throw at him. 

“Who is she?” Annie asked. 

Jeff and Britta turned to look at her. “What?” 

Annie hesitated but then said, “You’re obviously trying to impress someone. And it doesn’t seem to be working hence why you’re doing all this.” Annie gestured at him. “So, who is she?” 

Jeff opened his mouth to deny the whole thing, but then closed it again. Technically, yes, he was trying to impress someone. Though not for the reasons Annie thought and not a woman. 

“Finally found someone who doesn’t find you irresistible,” Britta teased. 

“Are you finally admitting that  _ you  _ find me irresistible?” Jeff shot back. 

“What? No! Shut up,” Britta replied.

“Great comeback. Now can I please have my glasses back,” Jeff asked.

“Give us a name,” Britta demanded. She looked so smug, holding the glasses behind her back. Jeff was not going to let her ruin this day for him. This was the day the Dean was going to faint because of his raw sexual appeal and Britta was not going to ruin that for him. 

He looked around the quad, not even knowing what he was looking for but needing something. Luckily, Garrett happened to be walking past them at that moment. He snatched the water bottle out of Garrett's hand and then poured it over his head making sure his chest was soaking by the end of it. He gave Garrett back the empty water bottle. “Thanks,” he said. He gave Britta a winning smile and then hurried off into the school. Their dumbfounded faces were hilarious. 

Jeff watched bemusedly as students and teachers alike stopped in their paths and gawked at him. More than one pair collided into each other or an open locker. He swore he saw someone faint as he walked by. All of this only made him quicken his step, sure that today he would be victorious. 

Jeff walked into the Dean’s office completely convinced that this was going to be a rousing success. The Dean and Frankie looked up as he entered and they both stared. But Jeff was completely focused on the Dean’s reaction. “Morning,” Jeff said, flashing them a smile. He watched as the Dean blinked rapidly. His eyes trailed down to Jeff’s chest, where he could feel the material of his shirt clinging to his muscles, leaving nothing to the imagination. The Dean’s mouth hung open as his eyes remained glued to Jeff’s chest. 

“What happened to you?” Frankie asked. The Dean looked over at Frankie when she spoke but Jeff kept his eyes on him. 

“Spilled some water,” Jeff replied. The Dean’s eyes returned to him. Jeff watched as his hand came up to tug at his tie, swallowing heavily. Then the Dean looked down at his desk. 

“Well, you should get changed, Jeffrey. Don’t want you catching a cold,” the Dean said. He cleared his voice, again tugging at his tie. He continued to stare down at his papers though. 

“Right,” Jeff replied, disheartened. Was the Dean really not going to look at him again? Jeff racked his brain for any idea to salvage this day. He walked up to the Dean’s desk, ignoring Frankie’s calculating gaze. Jeff placed one hand on the Dean’s desk and then leaned over to pluck a pen right next to the Dean’s hand. He held it up. “Mind if I borrow this? Forgot mine,” Jeff asked. He hadn’t meant to make his voice lower than usual but he was going with it. 

The Dean looked up at Jeff and then glanced back down at the pen and Jeff’s chest. 

“Of course,” he replied. His voice was high pitched and Jeff thought he finally got him when the Dean turned back to Frankie. “So, are you sure there’s no room in the budget for a dance next month?” 

Jeff didn’t let himself linger in the disappointment. The Dean was going to acknowledge his sexiness. Jeff was done playing nice. 

* * *

At some point, it should have occurred to Jeff that things had gotten out of hand. That point could have been when Neil brought out a grocery cart full of military grade water guns. Or it could have been after the fifth near drowning. Perhaps even once one of the inflatable water slides had popped, trapping several students for a total of three minutes before they were rescued. The point was that Jeff Winger did not seem to realize things had gotten out of hand. Nor had he noticed that his...outfit for the day had caused some of the incidents to occur.

So he was still calmly lounging on his beach chair, sipping his drink, when someone blocked his sun. Jeff opened an eye to see who the culprit was: Frankie. The furious look on her face was the first clue he had that maybe he’d crossed a line. 

“Frankie,” he began calmly. 

“Don’t,” Frankie snapped. “Do not even think about talking yourself out of this one. Look at what you’ve done!” 

Jeff knew that was meant to be rhetorical, but he had been lounging in his chair for a while. He looked out at the quad. The idea had been simple in theory. He spread the word that there would be a “spring break” themed party out on the quad. He didn’t have to do much from there. People brought inflatable pools, beach chairs, umbrellas; he was fairly certain there was a sandbox somewhere. But this was Greendale. Things had eventually gotten out of hand. There were big chunks of the quad that were completely flooded. This had obviously led to a mud fight that caused various walls and windows to end up covered in mud. And that wasn’t even taking into account the various students laying around in different degrees of consciousness and pain. 

Jeff looked back up at Frankie. He could attempt to explain this with the truth. But the truth was that he’d planned all of this so he could wear extremely small, and extremely inappropriate, skin tight swim trunks. The property damage and bodily harm inflicted were never in his plans. Though after more than five years at Greendale, he really should have known better. 

“You’re right,” Jeff said. “I shouldn’t have let things get out of hand. I’ll help you with all the clean up.” 

“No, what you’re going to do is go talk to the Dean,” Frankie said sternly. 

“What?” Jeff asked. Frankie would never let him off the hook so easily.

“I don’t know what it is you two are up to, whether you’re trying to spice things up in the bedroom or having a lovers quarrel, but I don’t care! The school nurse has submitted three complaints this week about being inundated with people having fainting spells or running into things because  _ you _ have decided to walk around here like a fucking sex god. So you are going to put on some clothes and go fix things with the Dean.” Frankie took a pause and as an afterthought added, “And then you’re going to come back and help me deal with this mess.” 

Jeff didn’t think he’d ever been this embarrassed in his adult life. He wasn’t even sure which part of Frankie’s speech was more humiliating. Spice things up in the bedroom? Was it that obvious to everyone that the Dean was the person Jeff was trying to impress? Actually, why did Frankie even think he and the Dean were-

“What are you standing around for? Go!” Frankie yelled at him. 

“Right,” Jeff said. He quickly gathered his clothes and shoes and started off in the direction of the Dean’s office. He’d correct Frankie later about what this was all really about. He had planned to get dressed as soon as he got into the building but then quickly scrapped that idea when he realized the flooding extending to the halls. He vaguely wondered if Frankie had seen this yet and whether the rest of the group was going to spend all weekend cleaning up his mess too. 

He arrived at the Dean’s door too soon. He still had no idea what he was going to say or do or why he still hadn’t gotten dressed despite the dry floor he was standing on. He could hear the Dean inside, talking frantically on the phone. Jeff took a moment to marvel at the fact that it hadn’t even occurred to him to go straight to his car and avoid all responsibility for this. Greendale had really changed him. 

Jeff let out a deep breath and turned into the office. The Dean was standing, back to the door. Jeff lightly knocked on the open door and the Dean held up a finger in the air without looking back. Jeff dropped all his clothes on the chair and silently closed the door. Whatever this conversation ended up being, it was probably best to be done in private. 

“Fine, fine, we will reimburse you the damages done to your rentals but please come and dispose of the ripped water slides...Thank you,” the Dean hung up the phone and turned. It wasn’t until that point that it occurred to Jeff what a bad idea this had been. Jeff was practically standing in the Dean’s office in nothing but underwear, with both doors closed. But even with that realization, Jeffrey was still not fast enough to catch the Dean before he fainted. 

Jeff rushed over to the Dean. He checked his head for bleeding but it looked like the fall hadn’t been that bad. Jeff took the Dean into his arms and moved him over to the couch. He shifted the throw pillows around till he thought the Dean was comfortable. Jeff knew he should go find someone. The Dean might need medical attention. For whatever reason, Jeff couldn’t stand the idea of leaving him alone. Actually, Jeff did know the reason. It was the same reason why he had become so obsessed with getting the Dean to flirt and touch him again. It was the same reason he had imagined punching Domingo’s pretty face. It must have been obvious to Frankie. How had she figured it out when they only knew each other for a few months and he’d known himself for 40 something years?

His inner monologue had apparently taken too long because the Dean was shifting on the couch. Jeff kneeled next to the Dean. He watched as the other man slowly opened his eyes and focused them on Jeff. “Hi,” Jeff said lamely. 

“Hi,” the Dean replied. His eyes moved downward and quickly flashed back up to his eyes. He watched the Dean swallow thickly and a light blush formed on his cheeks. “I take it you were at the pool party?”

“Yeah,” Jeff answered. And with Frankie’s voice ringing in his head, he added, “it was kinda my fault.” The Dean scrunched up with eyebrows and tilted his head to the side in the adorable way he did when something confused him. All the years of being a lawyer hadn’t prepared him for this. “I told everyone there was going to be a spring break themed party out on the quad today. Things...spiraled from there.” 

The Dean moved to sit up on the couch and leaned over to look Jeff in the eyes. “Jeffrey, if you wanted to have a pool party, you could’ve just asked.” 

“It wasn’t about the party,” Jeff began. Was he blushing? He couldn’t really remember the last time he’d blushed. “I was only looking for an excuse to wear...well, these.” Jeffrey gestured towards his crotch. The Dean glanced down and then quickly moved his eyes away. 

“Jeffrey, why do you think Greendale has so many themed events if not for me to wear an outfit?” 

Jeff stood up suddenly and walked towards the far wall. He ran his hand through his hair in frustration. “That’s not what I mean,” Jeff groaned. He was really going to spell it out, wasn’t he? He turned around to tell the Dean the truth, but he found the Dean’s eyes glued directly at his crotch. He watched as the Dean bit his bottom lip, eyes darker than they had been a second ago. “That!” Jeff yelled. The Dean jumped and looked up at him, startled. “That’s what I wanted.”

“You wanted people to stare at you,” the Dean asked. 

“No, I wanted  _ you  _ to stare at me.” 

Jeff fought every instinct in his body to run out of the room and drive to Salt Lake City and start a whole new life. Instead, he stood still and waited for the Dean to connect the dots. 

“I....I’m not following,” the Dean admitted. 

Jeff groaned. “You said that you were going to stop flirting and leering and touching me, right?” 

“Well, I don’t remember using the word ‘leering’-”

“Craig,” Jeff snapped. 

“Right, yes.”

“Well, I wasn’t happy with that. And I thought if I could have you break your promise, things would go back to normal.  _ We’d  _ go back to normal.”

The Dean opened and closed his mouth several times, seemingly rethinking everything he was going to say. “So…” he began, “you want me to...flirt with you?” 

“Yes,” Jeff answered. 

The Dean chuckled and looked down at the floor. “Because it boosts your ego to know that I am madly in love with you,” the Dean asked, throwing his hands out in exasperation. 

“Wait-”

“No!” the Dean yelled. He stood up and started gesticulating widely. “I finally get to a point where I can accept that you will never reciprocate my feelings and you come waltzing in here telling me that, actually, you do want me to throw myself at you on the daily so you can feel good about yourself.”

“That’s not-”

“Well, I have news for you Jeffrey Winger. It may have taken four different therapists and almost as many decades but I finally have some self respect and I won’t be at your beck and call any longer!”

“Can you just-”

“No, I refuse to give you preferential treatment for the hopes of you throwing me a bone here and-”

Jeff had heard enough. He grabbed the Dean’s- Craig’s- face and pressed his lips against the others harshly. The De-Craig melted into the kiss almost immediately. It was rough and sharp and made Jeff lightheaded. Craig’s arms moved around his bare back. Jeff mindlessly started leading them towards the couch, pushing his tongue past Craig’s willing lips. Craig fell backwards onto the couch and Jeff followed him, laying on top of him. 

Jeff pulled away momentarily to look down at Craig. His cheeks were flushed and he had a dazed look on his face. “I want you to flirt with me, but I think I also want you to date me,” Jeff said. He could feel Craig’s sharp intake of breath at Jeff’s declaration. This time it was Craig who smashed his lips against Jeff. Jeff leaned into the kiss, finally indulging in months of repressed longing. 

Craig moaned underneath him. His hands were roaming up and down Jeff’s back. Jeff was lost in the kiss. So much so that he didn’t realize he’d been grinding against Craig until their erections brushed against each other and they both groaned. 

“Fuck,” Jeff moaned. “Please tell me you don’t want to take this slow.” 

“Of course not!” Craig looked offended at the question. 

“Good,” Jeff said. He went back to kissing Craig as he moved his hand to unbuckle Craig’s pants. There was an embarrassing amount of fumbling but eventually Jeff’s hand wrapped around Craig’s dick. The feeling of another man’s penis in his hand was odd. But the noises and faces Craig was making as he began to pump him made Jeff’s brain short circuit. Jeff kissed and sucked at Craig’s neck, his hand getting used to the reversed angle. He ran his thumb over the head and was rewarded by a particularly lewd moan. 

Craig’s hands abandoned his back and moved down to his hips. They pulled down his tight swim trunks till Jeff’s dick was free. Craig’s hand slapped his away and he quickly brought both their cocks together and began pumping them at once. “God that feels good,” Jeff groaned. 

“Yes, yes, fuck,” Craig moaned below him. 

Jeff began pumping his hips in time with Craig’s strokes. “Tighter,” Jeff mumbled into Craig’s neck. Craig moaned and then tightened his grip on their dicks. “Shit, just like that,” Jeff praised. 

“Yes, Jeffrey, I-”

“Fuck, come for me, baby,” Jeff ordered. 

Craig instantly arched off the couch, his movements becoming frantic and moans falling off his lips. Watching Craig come undone like that pushed Jeff over the edge. He erratically ground his hips into Craig’s hip, coming all over his shirt. 

Jeff had enough mind to gently lay down against Craig, instead of collapsing on top of him. Craig’s arms wrapped around him. The moment was oddly peacefully and devoid of any major freak out. Jeff was sure it would come at some point but for now he was content to enjoy the afterglow. 

He wasn’t sure how long they’d laid there when there was a sharp pounding on the door. They both startled at the sound. 

“If you two are not dressed and outside of this office in five minutes, I am having the door removed for the rest of the year!” Frankie yelled through the door. 

Jeff and Craig shared a look and silently agreed that it would be a shame to forgo office sex so early in their relationship. They jumped off the couch and began scrambling for their clothes. Jeff got his pants on before searching Craig’s desk for a tissue to wipe off the cum on his chest. He looked over at the open closet door as Craig frantically searched for a plain shirt to wear within all the tulle and leather. 

“Is that a cowboy hat?” Jeff asked, peaking into the closet. 

“Cowgirl, technically,” Craig said, still searching. 

“Uh, I have a cowboy outfit,” Jeff said, his tone suggestive.

Craig stopped in his frantic searching and looked up at Jeff. “Really?” he asked, voice husky. 

“Yeah,” Jeff replied. He took a step towards Craig, images flashing through his head. 

“Two minutes!” Frankie warned. 

They both quickly started dressing again. There’d be time to finish that conversation later. 


End file.
